JP5653368B2 - 改善された貯蔵安定性を有する湿気硬化型シリル化ポリマー - Google Patents
改善された貯蔵安定性を有する湿気硬化型シリル化ポリマー Download PDFInfo
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- JP5653368B2 JP5653368B2 JP2011549306A JP2011549306A JP5653368B2 JP 5653368 B2 JP5653368 B2 JP 5653368B2 JP 2011549306 A JP2011549306 A JP 2011549306A JP 2011549306 A JP2011549306 A JP 2011549306A JP 5653368 B2 JP5653368 B2 JP 5653368B2
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- Prior art keywords
- silane
- moisture
- mole percent
- group
- silylated polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 title claims description 96
- 238000003860 storage Methods 0.000 title description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 115
- 229910000077 silane Inorganic materials 0.000 claims description 75
- -1 2-isocyanatoethylmethoxydiethoxysilane Silane Chemical compound 0.000 claims description 40
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 27
- 239000000376 reactant Substances 0.000 claims description 23
- 238000006884 silylation reaction Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 14
- 239000000565 sealant Substances 0.000 claims description 13
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 12
- 230000001070 adhesive effect Effects 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 11
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 150000004756 silanes Chemical class 0.000 claims description 11
- 239000000945 filler Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000002318 adhesion promoter Substances 0.000 claims description 6
- 239000008199 coating composition Substances 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- IVJJAJZLEWCWMI-UHFFFAOYSA-N diethoxy-(3-isocyanatopropyl)-methoxysilane Chemical compound CCO[Si](OCC)(OC)CCCN=C=O IVJJAJZLEWCWMI-UHFFFAOYSA-N 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 239000013008 thixotropic agent Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000005060 rubber Substances 0.000 claims description 4
- JQKBYCKXGRPGAV-UHFFFAOYSA-N 3-isocyanatopropyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCN=C=O JQKBYCKXGRPGAV-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000013008 moisture curing Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- VWVDXQYGCFFQEB-UHFFFAOYSA-N 2,2-dimethoxyethoxy(3-isocyanatopropyl)silane Chemical compound N(=C=O)CCC[SiH2]OCC(OC)OC VWVDXQYGCFFQEB-UHFFFAOYSA-N 0.000 claims description 2
- DQKJNMYIIVPNPU-UHFFFAOYSA-N 2,2-dimethoxyethoxy(isocyanatomethyl)silane Chemical compound N(=C=O)C[SiH2]OCC(OC)OC DQKJNMYIIVPNPU-UHFFFAOYSA-N 0.000 claims description 2
- IHZHYITXFSSZIZ-UHFFFAOYSA-N 2-isocyanatoethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCN=C=O IHZHYITXFSSZIZ-UHFFFAOYSA-N 0.000 claims description 2
- AQSKFYRGZPZSEX-UHFFFAOYSA-N 3-isocyanatopropyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)CCCN=C=O AQSKFYRGZPZSEX-UHFFFAOYSA-N 0.000 claims description 2
- QRDUJPPXBPTAIQ-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-(2-methylpropoxy)silane Chemical compound CC(C)CO[Si](OC)(OC)CCCN=C=O QRDUJPPXBPTAIQ-UHFFFAOYSA-N 0.000 claims description 2
- UHWMQDAVSDKCGD-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-propan-2-yloxysilane Chemical compound CC(C)O[Si](OC)(OC)CCCN=C=O UHWMQDAVSDKCGD-UHFFFAOYSA-N 0.000 claims description 2
- LAZFDDOLNZQDOE-UHFFFAOYSA-N 3-isocyanatopropyl-dimethoxy-propoxysilane Chemical compound CCCO[Si](OC)(OC)CCCN=C=O LAZFDDOLNZQDOE-UHFFFAOYSA-N 0.000 claims description 2
- IATVEYUMCJAPTF-UHFFFAOYSA-N 3-isocyanatopropyl-methoxy-bis(2-methylpropoxy)silane Chemical compound CC(C)CO[Si](OCC(C)C)(OC)CCCN=C=O IATVEYUMCJAPTF-UHFFFAOYSA-N 0.000 claims description 2
- RAGWTBZZWJGPGR-UHFFFAOYSA-N 3-isocyanatopropyl-methoxy-dipropoxysilane Chemical compound CCCO[Si](OCCC)(OC)CCCN=C=O RAGWTBZZWJGPGR-UHFFFAOYSA-N 0.000 claims description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- WPLLHIDHPZDIJX-UHFFFAOYSA-N butan-2-yloxy-(3-isocyanatopropyl)-dimethoxysilane Chemical compound CCC(C)O[Si](OC)(OC)CCCN=C=O WPLLHIDHPZDIJX-UHFFFAOYSA-N 0.000 claims description 2
- YSQLMVHSQRWYBO-UHFFFAOYSA-N butoxy-(3-isocyanatopropyl)-dimethoxysilane Chemical compound CCCCO[Si](OC)(OC)CCCN=C=O YSQLMVHSQRWYBO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003431 cross linking reagent Substances 0.000 claims description 2
- PBPWOJWEWAPHRO-UHFFFAOYSA-N diethoxy-(isocyanatomethyl)-methoxysilane Chemical compound CCO[Si](OCC)(OC)CN=C=O PBPWOJWEWAPHRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- NPBAOMZPNKFOIP-UHFFFAOYSA-N tri(butan-2-yloxy)-(3-isocyanatopropyl)silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)CCCN=C=O NPBAOMZPNKFOIP-UHFFFAOYSA-N 0.000 claims description 2
- VPRMDTDSWWDQHO-UHFFFAOYSA-N tributoxy(3-isocyanatopropyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCN=C=O VPRMDTDSWWDQHO-UHFFFAOYSA-N 0.000 claims description 2
- KEIBTGABMNALIT-UHFFFAOYSA-N triethoxy(2-isocyanatoethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCN=C=O KEIBTGABMNALIT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 2
- LSXVLBRBTWJXKC-UHFFFAOYSA-N 3-isocyanatopropyl-methoxy-di(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC)CCCN=C=O LSXVLBRBTWJXKC-UHFFFAOYSA-N 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- WXGNPLOJWLOIIC-UHFFFAOYSA-N di(butan-2-yloxy)-(3-isocyanatopropyl)-methoxysilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC)CCCN=C=O WXGNPLOJWLOIIC-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000013618 particulate matter Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 claims 1
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 94
- 238000006243 chemical reaction Methods 0.000 description 25
- 229920005862 polyol Polymers 0.000 description 24
- 150000003077 polyols Chemical class 0.000 description 20
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229920002635 polyurethane Polymers 0.000 description 12
- 239000004814 polyurethane Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000013500 performance material Substances 0.000 description 10
- 239000005056 polyisocyanate Substances 0.000 description 9
- 229920001228 polyisocyanate Polymers 0.000 description 9
- 239000002243 precursor Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 229910052718 tin Inorganic materials 0.000 description 8
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- 238000001723 curing Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- AVRBSCLVFWGLFA-UHFFFAOYSA-N 3-(2,2-dimethoxyethoxysilyl)propan-1-amine Chemical compound NCCC[SiH2]OCC(OC)OC AVRBSCLVFWGLFA-UHFFFAOYSA-N 0.000 description 4
- XYWBBDSPFGNYOJ-UHFFFAOYSA-N 3-[diethoxy(methoxy)silyl]propan-1-amine Chemical compound CCO[Si](OCC)(OC)CCCN XYWBBDSPFGNYOJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical class [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 4
- 239000011236 particulate material Substances 0.000 description 4
- 239000013589 supplement Substances 0.000 description 4
- 150000003606 tin compounds Chemical class 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000005370 alkoxysilyl group Chemical group 0.000 description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 description 2
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical compound NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- GKYGYWOJHVZUTN-UHFFFAOYSA-N (1-methyl-6-triethoxysilylcyclohexa-2,4-dien-1-yl)methanethiol Chemical compound CCO[Si](OCC)(OCC)C1C=CC=CC1(C)CS GKYGYWOJHVZUTN-UHFFFAOYSA-N 0.000 description 1
- RKBANWCUDWRSJO-UHFFFAOYSA-N (1-methyl-6-trimethoxysilylcyclohexa-2,4-dien-1-yl)methanethiol Chemical compound CO[Si](OC)(OC)C1C=CC=CC1(C)CS RKBANWCUDWRSJO-UHFFFAOYSA-N 0.000 description 1
- SOYSVTBJISWJGW-UHFFFAOYSA-N 12-(2,2-dimethoxyethoxysilyl)dodecane-1-thiol Chemical compound SCCCCCCCCCCCC[SiH2]OCC(OC)OC SOYSVTBJISWJGW-UHFFFAOYSA-N 0.000 description 1
- MOBUVILYZWQWRZ-UHFFFAOYSA-N 12-[diethoxy(methoxy)silyl]dodecane-1-thiol Chemical compound CCO[Si](OCC)(OC)CCCCCCCCCCCCS MOBUVILYZWQWRZ-UHFFFAOYSA-N 0.000 description 1
- LAGFJUQEHPLLIW-UHFFFAOYSA-N 12-triethoxysilyldodecane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCCCCCS LAGFJUQEHPLLIW-UHFFFAOYSA-N 0.000 description 1
- VREPHMROZZKOOL-UHFFFAOYSA-N 12-trimethoxysilyldodecane-1-thiol Chemical compound CO[Si](OC)(OC)CCCCCCCCCCCCS VREPHMROZZKOOL-UHFFFAOYSA-N 0.000 description 1
- IKOPJOGLZWEOFM-UHFFFAOYSA-N 18-(2,2-dimethoxyethoxysilyl)octadecane-1-thiol Chemical compound SCCCCCCCCCCCCCCCCCC[SiH2]OCC(OC)OC IKOPJOGLZWEOFM-UHFFFAOYSA-N 0.000 description 1
- VTNJMNBJRQLNGK-UHFFFAOYSA-N 18-[diethoxy(methoxy)silyl]octadecane-1-thiol Chemical compound CCO[Si](OCC)(OC)CCCCCCCCCCCCCCCCCCS VTNJMNBJRQLNGK-UHFFFAOYSA-N 0.000 description 1
- UAXHQOHEACNJSR-UHFFFAOYSA-N 18-trimethoxysilyloctadecane-1-thiol Chemical compound CO[Si](OC)(OC)CCCCCCCCCCCCCCCCCCS UAXHQOHEACNJSR-UHFFFAOYSA-N 0.000 description 1
- HXVHPNWGIUITGP-UHFFFAOYSA-N 18-tripropoxysilyloctadecane-1-thiol Chemical compound CCCO[Si](OCCC)(OCCC)CCCCCCCCCCCCCCCCCCS HXVHPNWGIUITGP-UHFFFAOYSA-N 0.000 description 1
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- GHRVWAUKHHCFER-UHFFFAOYSA-N dibutyl 2-(triethoxysilylmethylamino)butanedioate Chemical compound CCCCOC(=O)CC(NC[Si](OCC)(OCC)OCC)C(=O)OCCCC GHRVWAUKHHCFER-UHFFFAOYSA-N 0.000 description 1
- ODJZQCGUABNDLD-UHFFFAOYSA-N dibutyl 2-(trimethoxysilylmethylamino)butanedioate Chemical compound CCCCOC(=O)CC(NC[Si](OC)(OC)OC)C(=O)OCCCC ODJZQCGUABNDLD-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical class CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- XYTLYCKMLUDWPP-UHFFFAOYSA-N n,2-dimethyl-3-triethoxysilylpropan-1-amine Chemical compound CCO[Si](OCC)(OCC)CC(C)CNC XYTLYCKMLUDWPP-UHFFFAOYSA-N 0.000 description 1
- SMIDUPHNWFRONB-UHFFFAOYSA-N n,2-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCC(C)C[Si](OC)(OC)OC SMIDUPHNWFRONB-UHFFFAOYSA-N 0.000 description 1
- KFOZMMAXUUCIKU-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OCC)(OCC)OCC KFOZMMAXUUCIKU-UHFFFAOYSA-N 0.000 description 1
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 1
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- RUTBGEATFXGNSD-UHFFFAOYSA-N n-[3-[diethoxy(methoxy)silyl]propyl]cyclohexanamine Chemical compound CCO[Si](OCC)(OC)CCCNC1CCCCC1 RUTBGEATFXGNSD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- PNAUMDBGSPRGCS-UHFFFAOYSA-N n-ethyl-2-methyl-3-triethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OCC)(OCC)OCC PNAUMDBGSPRGCS-UHFFFAOYSA-N 0.000 description 1
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 description 1
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- NPBGADJIQDWENZ-UHFFFAOYSA-N n-methyl-2-(3-tripropoxysilylpropoxy)propan-1-amine Chemical compound CCCO[Si](OCCC)(OCCC)CCCOC(C)CNC NPBGADJIQDWENZ-UHFFFAOYSA-N 0.000 description 1
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- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000003707 silyl modified polymer Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- RHCQSXFNFRBOMC-UHFFFAOYSA-N triethoxysilylmethylurea Chemical compound CCO[Si](OCC)(OCC)CNC(N)=O RHCQSXFNFRBOMC-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- UOTGHAMTHYCXIM-UHFFFAOYSA-N trimethoxysilylmethylurea Chemical compound CO[Si](OC)(OC)CNC(N)=O UOTGHAMTHYCXIM-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- 229910052882 wollastonite Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Silicon Polymers (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/322,882 US8138297B2 (en) | 2009-02-09 | 2009-02-09 | Moisture-curable silylated polymer possessing improved storage stability |
| US12/322,882 | 2009-02-09 | ||
| PCT/US2010/023456 WO2010091338A1 (en) | 2009-02-09 | 2010-02-08 | Moisture-curable silylated polymer possessing improved storage stability |
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| JP2012517505A JP2012517505A (ja) | 2012-08-02 |
| JP2012517505A5 JP2012517505A5 (enExample) | 2013-03-28 |
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| JP (1) | JP5653368B2 (enExample) |
| CN (1) | CN102361901B (enExample) |
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| WO (1) | WO2010091338A1 (enExample) |
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| CN104583222A (zh) * | 2012-09-04 | 2015-04-29 | 拜耳材料科技股份有限公司 | 具有硫代氨基甲酸酯结构的异氰酸根合硅烷 |
| CN105579484B (zh) * | 2013-02-26 | 2019-06-04 | 霍尼韦尔国际公司 | 含有卤代烯烃发泡剂的聚氨酯泡沫预混物和由其制造的泡沫 |
| CN103436216B (zh) * | 2013-09-05 | 2014-12-31 | 江苏天辰新材料有限公司 | 一种脱醇型低模量高伸长率的有机硅密封胶及其制备方法 |
| CN103509517B (zh) * | 2013-09-05 | 2015-10-28 | 江苏天辰硅材料有限公司 | 一种瓷化阻燃防火硅酮密封胶及其制备方法 |
| CN103436217A (zh) * | 2013-09-06 | 2013-12-11 | 江苏天辰硅材料有限公司 | 一种单组份脱醇型耐油硅酮密封胶及其制备方法 |
| CN103602306B (zh) * | 2013-09-06 | 2016-01-20 | 江苏天辰新材料股份有限公司 | 一种单组份室温硫化透明脱醇型防霉硅酮密封胶及其制备方法 |
| US9321878B2 (en) * | 2013-12-16 | 2016-04-26 | Momentive Performance Materials Inc. | Process for the preparation of silylated polyurethane polymers using titanium-containing and zirconium-containing catalysts |
| US20150203624A1 (en) * | 2014-01-21 | 2015-07-23 | Vladimyr Wolan | Second generation hybrid silane modified polymers of low viscosity for low toxicity rtv sealants and adhesives |
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| FR3068633B1 (fr) * | 2017-07-04 | 2019-08-23 | Bostik Sa | Preparation d'une composition adhesive dans une extrudeuse |
| EP3565857B1 (de) * | 2017-12-15 | 2020-03-25 | Wacker Chemie AG | Vernetzbare massen auf der basis von organyloxygruppen aufweisenden organopolysiloxanen |
| CA3113952C (en) | 2018-09-24 | 2023-09-19 | Building Materials Investment Corporation | Roofing membranes with improved adhesive bonding strength |
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| CN112142945B (zh) * | 2019-06-27 | 2022-07-12 | 万华化学集团股份有限公司 | 一种高稳定性的端硅烷基聚合物树脂及其制备方法 |
| EP4110842B1 (en) | 2020-02-26 | 2024-02-07 | Akzo Nobel Coatings International B.V. | Alkoxysilane functional polyurethane-urea for adhesive or coating |
| JP2023519822A (ja) * | 2020-04-08 | 2023-05-15 | シーカ テクノロジー アクチェンゲゼルシャフト | 向上された上塗り性を有するシラン官能性ポリマーをベースとする組成物 |
| KR102820691B1 (ko) * | 2020-06-24 | 2025-06-12 | 와커 헤미 아게 | 수분-경화 컨포멀 코팅 조성물 |
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| CN114574155A (zh) * | 2021-12-17 | 2022-06-03 | 浙江新安化工集团股份有限公司 | 一种安全环保型单组份橡皮泥状硅酮密封胶及其制备方法 |
| CN114479741B (zh) * | 2022-02-23 | 2023-03-31 | 广州市白云化工实业有限公司 | 一种低温可快速深层固化的单组分有机硅改性密封胶及其制备方法 |
| CN119053644A (zh) | 2022-05-04 | 2024-11-29 | 美国陶氏有机硅公司 | 硅酮-聚醚共聚物、包含硅酮-聚醚共聚物的密封剂和相关方法 |
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-
2009
- 2009-02-09 US US12/322,882 patent/US8138297B2/en not_active Expired - Fee Related
-
2010
- 2010-02-08 WO PCT/US2010/023456 patent/WO2010091338A1/en not_active Ceased
- 2010-02-08 JP JP2011549306A patent/JP5653368B2/ja not_active Expired - Fee Related
- 2010-02-08 CN CN201080013146.XA patent/CN102361901B/zh not_active Expired - Fee Related
- 2010-02-08 EP EP10703778.0A patent/EP2393861B1/en not_active Not-in-force
- 2010-02-08 BR BRPI1007886-0A patent/BRPI1007886B1/pt active IP Right Grant
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| Publication number | Publication date |
|---|---|
| EP2393861A1 (en) | 2011-12-14 |
| BRPI1007886A2 (pt) | 2017-01-17 |
| CN102361901A (zh) | 2012-02-22 |
| US20100204384A1 (en) | 2010-08-12 |
| WO2010091338A1 (en) | 2010-08-12 |
| EP2393861B1 (en) | 2013-10-23 |
| CN102361901B (zh) | 2014-06-11 |
| JP2012517505A (ja) | 2012-08-02 |
| BRPI1007886B1 (pt) | 2020-02-11 |
| US8138297B2 (en) | 2012-03-20 |
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